Lithium diisopropylamide → HCID 67432981、化合物

HRID 1040202ノート

反応式

HRID 1040202 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([NH:13][C:14]2[N:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][N:15]=2)[CH:5]=[C:6]([C:8]2[S:12][CH:11]=[N:10][CH:9]=2)[CH:7]=1.[Li+].CC([N-]C(C)C)C.[CH3:32][C:33]1([CH3:44])[C:42](=[O:43])[CH2:41][CH2:40][CH2:39][C:34]21[O:38][CH2:37][CH2:36][O:35]2>C1COCC1.[Cl-].[NH4+]>[CH3:32][C:33]1([CH3:44])[C:42]([C:11]2[S:12][C:8]([C:6]3[CH:5]=[C:4]([NH:13][C:14]4[N:19]=[C:18]([C:20]([F:21])([F:23])[F:22])[CH:17]=[CH:16][N:15]=4)[CH:3]=[C:2]([CH3:1])[CH:7]=3)=[CH:9][N:10]=2)([OH:43])[CH2:41][CH2:40][CH2:39][C:34]21[O:35][CH2:36][CH2:37][O:38]2

参加物

6

反応物 3

HCID 2724682Lithium diisopropylamideHCID 109977176,6-dimethyl-1,4-dioxaspiro[4.5]decan-7-oneHCID 58456403N-[3-methyl-5-(1,3-thiazol-5-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine

生成物 1

HCID 67432981HCID 67432981、化合物収率 57.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 25517Ammonium Chloride溶媒

実験手順

To a stirred solution of INTERMEDIATE 4 (1.09 g, 3.24 mmol) in THF (17 mL) was added LDA (2M, 4.86 mL, 9.72 mmol) dropwise at −78° C. The orange solution was left to stir for 30 min at that temperature, treated with 6,6-dimethyl-1,4-dioxaspiro[4.5]decan-7-one (0.72 g, 3.9 mmol) in THF (4.5 mL) dropwise, and allowed to warm to room temperature as the bath did. The reaction mixture was diluted with saturated ammonium chloride solution, and extracted with EtOAc (3×). The combined organics were washed with brine, dried (sodium sulfate), filtered concentrated, and purified by column chromatography on silica to afford 6,6-dimethyl-7-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]-1,4-dioxaspiro[4.5]decan-7-ol (964 mg, 1.85 mmol) as a light yellow foam. MS ESI: [M+H]+ m/z 521.1.

後処理

  1. waitThe orange solution was left
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organics were washed with brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography on silica

出典と根拠

ORDレコード
ord-9d45d762adf94cb690d67d9e4cc19925
出典データセット
uspto-grants-2013_10
特許番号
US08551984B2

反応ノート

読み込み中…